Azo dyestuffs insoluble in water and fiber dyed therewith



wherein X stands for alkyl, for halogen and Patented :Nov. 14, 1933 AND FIBER DYED "IIHEREWITH j Otto Solist, deceased, late of Franlxlort-on the A ministratrix,

, I Main-'Hoehst. Germany, by Adele Sohst, ad- I Frankfort-on-theaMainflochst,=

. Germany, assignor toj General Aniline"-. Works',-

. Inc.,- N ew York, Y., a corporation-of Dela- .ware

No Drawing- KppIicatiOn Jul 1930 Serial I No; (111,429; and'in Gern any August 1 1929 v I I I 0 s; (Oi. '260 95 -3 I The present invention relates to valuable new sodium carbonate in one liter, well rinsed again and dried. V a

azo dyestufis, insoluble in water,' .andto Ifiber dyed therewith; more particularly it relates to azo dyestuifsof the following general formula: I

' R for a radical of the benzene series'which does not contain a sulfonic or a carboxylic acid group.

( Grounding Zi of; .5

I lgf r 2 3 hydroxynaphthoyl 4 methyl 2 55 Inethoxy 5'-chloro-1- -aminobenzene.

" 8. cc. of 'Turkey red oil'of.50% strength and 8 fcci. of caustic soda solution of 34 B are .c lissIolvedin boiling water; after cool- 'ing to about 50C..

' :4 cc. of a solution of formaldehyde of strength are added and the whole is 'made up with water to r v .The new dyestufisareobtainable. by coupling 1000 with a 2'.3'-hydroxy-naphthoylaminoehalogen cresolether of the following general forniula V I (b) Dyebath I invention, but they are not intended to'limit it 1 ,8 g. of. the-hydrochloride of 4-c hloro-2 whereinX stands for alkyl and l-llg -for-halogenf 3a diazo compound of the benzene series'which does not contain asulfonic group or a carboxylic 1 thereto, the parts being by weight:

Example 1 gr. of boiled cotton yarn are treated with the grounding'liquor forabout hour, hydro- 'Ihe dyest fis inaybe prepared;in severalways,- I I U I I There is obtained a brilliant Turkey red dyeing methyl l-amino-benzene are diazo- 0 I "tized with. I 1;}8 cc.fof hydrochloric acid of '22" Be. and 0, g. of dissolved sodium nitrite. -The solu-' tionis neutralized withabout c a 2 'g.-' of dissolved sodium acetate, 75 25 g1: of sodium chloride are addedand the whole is made up withwaterto with'good'fastnessproperties tojchlorine, to boil- 7 ing lye,-to.kier boilingand to light.

By, subst'tuting for the hydrochloride of '4- chIorO-Z-methyl-l-amino-benzene, ;used 'in the above examp1e,.the same quantityof 5-ch1oro-2-' inethyl-l-an inmbenzene, a scarlet dyeing of th same fastnes's properties 'is obtained.

extracted or squeezed, developed in the dye-bath during about 1 hour, rinsed, soaped in a boiling I soap bath containing 3 gr.'of soap and l grof Example 2 (a)'Grotmdihgliquorls the sameas described; t in'Examplel. i

(b).Dyebath: 7 2,2 g. of 4-bromo-5-chloro-2-methyl-1-ami-' I no-benzene are diazotized with 3,8 ccfoflhydrochloric acid and I 0, 75 g of dissolved sodium nitrite. .The soluis neutralized with about of sodium acetate and about 1 g. of dissolved sodium bicarbonate, 25 g. of sodium chloride are added and the whole is made up with Water to There is obtained a vivid Turkey red dyeing having the same fastness properties as the dyeing of Example 1 has.

Example 3 v (a) Grounding liquor of 4 g. of 2'3-hydroXynaphthoy1-2-methy 5-methoxy-4-chloro-l-amino-benzene is prepared as described in Example 1. (b) Dyebath: r

1,6 g. of the hydrochloride "of asymmetrical m-xylidine are diazotized with 1, 8 cc. of hydrochloric acid of 223.31%. and 0, '75 g of sodium nitrite. The solution is neutralized with about 1 g. of sodium bicarbonate;- 3 w 25 g. of sodium chloride are'added and the whole is made up with Wate r'to' wherein X stands for alkyl, Hlg, for halogen and R for a radical of the benzene series, being in the dry state red to bluish-red powders having as pigments a good fastness to light and on the fiber a satisfactory fastness to kier boiling and a'very good fastness'to light.

2. The azo dyestufis, insoluble in water, of the following general formula:

wherein the two Xs stand for alkyl, I-Ilg for halogen, -Y. for hydrogen or halogen and Z for alkyl or halogen, being in the dry state redyellowish powders, having as pigments a good fastness to light and on the fiber a satisfactory fastness to kier boiling and a very good fastness tolight.

3. The azodyestufi, insoluble in water, of the following probable formula:

being inthe state a yellowish-red powder having aspigment-a'g'ood fastness to light and on the fiber a satisfactory fastness to kier boiling and a very good fastness to light.

4. Fiber dyed with the azo dyestuffs, claimed in claim 1. a

5. Fiber dyed with the azo dyestuffs, claimed inclain12. J r 6. Fiber dyed with the azo dyestufi, claimed in claim3.

7; The azo 'dyestufi, insoluble in water, of the following probable formula:

yielding when produced on the'fiber a brilliant Turkey red dyeing of good fa'stness properties to kier boiling and to light. I

8; The azo dyestufi,'insoluble in water, of the following probable formula:

yielding whenproduced on the fiber a vivid Turkey red dyeing of good fastness properties to chlorine, kier boiling and to light.

9. Fiber dyed with the azo dyestufi claimed in claim 10. Fiber dyed with the azo dyestufi claimed in claim 8. 7 v

' j 'ADELE SOHST,

Administratrix of 0tto S0hst, Deceased. 

